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I3750

Sigma-Aldrich

3-Indolessigsäure

98%

Synonym(e):

Heteroauxin, IAA

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5 G
CHF 25.90
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About This Item

Empirische Formel (Hill-System):
C10H9NO2
CAS-Nummer:
87-51-4
Molekulargewicht:
175.18
Beilstein:
143358
EG-Nummer:
201-748-2
MDL-Nummer:
MFCD00005636
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24896043
NACRES:
NA.22

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Assay

98%

mp (Schmelzpunkt)

165-169 °C (lit.)

SMILES String

OC(=O)Cc1c[nH]c2ccccc12

InChI

1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)

InChIKey

SEOVTRFCIGRIMH-UHFFFAOYSA-N

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Allgemeine Beschreibung

3-Indoleacetic acid (IAA) is a naturally occurring hydrophilic organic compound consists of an unsaturated aromatic ring that is commonly used in the synthesis of indolylated diarylmethanes, α-acetoxyl ketones, and Indolmethyl-Chromones via copper catalyzed coupling reactions. [1] [2] [3] [4]

Anwendung

3-Indoleacetic acid (IAA) can be used as a building block to synthesize ,(±) harmacine using 4,4-diethoxybutan-1-amine via an acid-catalyzed acyl iminium ion cyclization reaction.
(±)-Harmacine is a vital step in the synthesis of a variety of indole alkaloids and dopamine/serotonin receptor ligands.[5] IAA can also be used in the preparation of alkaloid (±)-19-hydroxyibogamine.[6]

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
0000431176
0000431176
BCCL4942
BCCM4946
BCCL1887

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Die Dokumentenbibliothek aufrufen

Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Sulfoxonium Ylides for the Synthesis of alpha-Acetoxyl Ketones
Qiwen G, et al.
Organic Letters, 26, 5940-5945 (2024)
Effects of exogenous 3-indoleacetic acid and cadmium stress on the physiological and biochemical characteristics of Cinnamomum camphora
Jihai Z, et al.
Ecotoxicology and Environmental Safety, 191, 109998-109998 (2020)
A novel synthesis of (?)-harmacine and (?) 1, 2, 3, 4, 6, 7, 12, 12b-octahydroindole [2, 3-a] quinolizine
King Frank D
Journal of Heterocyclic Chemistry, 44(6), 1459-1463 (2007)
Copper-Mediated Cyclization of o-Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones
Kangmei W, et al.
The Journal of Organic Chemistry, 87, 9270-9281 (2022)
Microwave-assisted copper catalyzed decarboxylative reductive coupling of para-quinone methides with 3-indoleacetic acids: rapid access to polycyclic spiroindolequinone derivatives
Gui-Ting S, et al.
Inorganic chemistry frontiers, 10, 1512-1520 (2023)
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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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